Product Q&A: managing external expectations of the product roadmap

First Round Capital has a wonderful online network, basically a white-labelled quora, for people at their portfolio companies. While I was with their portfolio company Axial, I answered a number of questions. I’m sharing some of the Q’s I have answered over the last year or two:

How do you best manage expectations/predictability when interfacing (roadmap, status updates, etc) with the company outside of product development?

With our (Axial’s) B2B online marketplace, we don’t have to make commitments to customers long beforehand, so our roadmap can stay pretty flexible. That isn’t the case for every B2B product. We take advantage of that freedom because we are constantly tweaking our roadmap based on what we’re learning. Our answer to your question has been three-fold: a lot of externalization, a lot of interaction, and finally, building trust in both our pace of delivery and our decisions.

For externalization and interaction, we try to run brainstorming sessions with the different teams (customer success, sales, etc) every few months so that teams feel heard. We write an internal blog post almost every week that talks about what is being worked on, why, and any roadmap changes, and why. We also publish important research findings, metrics or experiments. Not everyone reads everything, but by not being a black box, we build trust. We also constantly try to draw lines back to the key “north star” goals/OKRs of the business. And we’re quick to respond to bug reports and questions. Again, no black box.

We do set expectations around timing, and we view those as goals but not hard promises. The team has learned that we’re pretty good within the next 2-3 months, but anything can change beyond that time period. It helps that we have a culture that buys into shipping things that have *impact* rather than sheer code output — even when that impact is sometimes more qualitative than quantitative.

Finally, we’ve been able to create room for flexibility because 1. our colleagues know that we agonize over what to work on with our limited throughput, and 2. because we ship every week, multiple times a week, and so it feels like we’re making continual progress.

There’s no freakout if something slips, not because everyone really gets the true complexity of software (they don’t), but because there is trust and our teammates now give the prod-eng team the benefit of the doubt.

What’s your favorite tool for product roadmaps if you already have a ticket tracking system?

Our toolset is constantly evolving but currently:

Trello to manage the roadmap from a high-level business perspective, including the goals and experiments we want to run. In my experience it is necessary to have a place for people to go look, but most don’t actually do so.

Jotto, an internal blog, to share weekly updates on quarterly OKRs, what is in the works and soon to ship, evolutions in strategy, interesting metrics, interesting external research notes, results and iterations of recent product initiatives, etc across the company

Google Slides to actually edit/manage the OKR sheets (we have used the OKR quadrant Wodtke talks about in her book Radical Focus) – but this is more internal to the team

Pivotal Tracker to manage our in-the-weeds work across the different teams (again internal to product/engineering team)

A wiki for technical/engineering documentation (internal to prod-eng team)

Some of the most important work is the lo-fi / lo-tech stuff, doing collaborative sketching (design studios), bi-weekly qualitative feedback/research reviews, roadmap planning sessions etc with different groups across the company. For major roadmap updates, there is a larger presentation across the company.

We use Google Sheets if we are doing impact/effort/risk weightings across different ideas, and Excel for larger, more complex modeling

One exercise I recently ran was as simple as writing down all the lurking product ideas on 50+ white index cards and having each team do their own force-rank card sort. It’s much easier for people when it’s tactile, but that does require the group being in the same room. All the teams could see the results of the other teams (as simple as sharing the photograph of the final card sort on Jotto). To be clear – we didn’t make the final roadmap a democratic process, but the product team appreciated hearing the different perspectives and everyone appreciated being heard. If you do something like this, it’s often worth doing a separate one with the executive team.

Regardless of the tools, it just takes a lot of engagement and repetition.